Cozumel’s main beachfront avenue, Rafael Melgar, is decorated with sculptures commemorating events in Cozumel's history. Most notably is the Monument of Two Cultures, also known as the Mestizo Monument. It depicts Gonzalo Guerrero who has become a political and literary icon and has been transformed into a national myth.

Guerrero, a sailor from Spain, and Jerónimo de Aguilar who had taken holy orders in his native Spain, were shipwrecked along the Yucatan Peninsula. All of the surviving crew of Spanish explorer Valdivia's vessel were taken as slaves by the local Maya including Guerrero and Aguilar. Some of the crew managed to escape ocassionally but were soon captured by other Mayan lords, who also enslaved them. After some time the only survivors were Aguilar and Guerrero. These two Spanish shipwreck survivors became the first Europeans to penetrate the mysteries of the Maya culture as they found it, still free from all contact with the West.

Guerrero assimilated into the Mayan culture, learning the language and adopting Mayan ways. He earned his freedom, became a respected warrior under Nachan Kaan, Lord of Chektumal, married his daughter and fathered her three children, which became the first Mestizos. Mestizo is a Spanish term that continues to be used today in Latin America to refer to people of mixed European (Spaniard) and Amerindian ancestry living in the region of Latin America. Fray Jerónimo de Aguilar remained true to his priestly vows and refused to form a romantic liaison with any of the attractive girls whom the chief placed at his disposal but was allowed to remain alive as a slave.

On Holy Cross Day (May 3rd), 1518 an expedition led by Juan de Grijalva landed in Cozumel. During three days the Spaniards circled the island, and the 6th of May, 1518, they found safe harbor next to what is now San Miguel, where they expected to find resistance, but were received in peace, and were surprised to see the first building made of stone in the new world. The islanders traded with the Spaniards, exchanging gold and a variety of goods. The Catholic mass held that day on the beach which is now known as Playa Las Casitas (little houses), is still celebrated by locals every year.

Upon his return to Cuba, Juan de Grijalva brought news about the existence of two Spaniards in the land of the Yucatán. When Hernán Cortés arrived in Cozumel in command of the next expedition in 1519, he sent Guerrero and Aguilar word to join him on the island. Fray Jerónimo de Aguilar did so after a few days, but Gonzalo Guerrero sent word back refusing to return with the Spaniards.

Aguilar spoke to Guerrero, reminding him that he was of Christian faith and should not throw away his everlasting soul for the sake of an Indian woman, but Gonzalo was not to be convinced. Guerrero’s response is inscribed on a plaque at the monument, and the translation is: "Brother Aguilar; I am married and have three children, and they look on me as a cacique (lord) here, and captain in time of war. My face is tattooed and my ears are pierced. What would the Spaniards say if they saw me like this? Go and God's blessing be with you, for you have seen how handsome these children of mine are.”

Francisco de Montejo had joined Grijalva’s expedition and was in command of four ships. After discovering Guerrero’s respected position with the Mayans, Montejo tried to win over Guerrero by sending him a long letter, again reminding him of his Christian faith, offering him his friendship and a complete pardon. Guerrero refused to join his countrymen and furthermore set about organizing the Mayans so that they could defend their land from the Spanish takeover. Guerrero was later killed while fighting on the side of the Indians against the Spaniards.

was the first site touched by the Spanish army of Hernán Cortés in what is now Mexican territory thus becoming the starting point for Spain's conquest of Mexico.